Chad DiNenna won't say the word. It's as if someone were
standing by with a bar of Safeguard, ready to wash out his mouth.
"We, uh, don't like to use that word around
here," says DiNenna, 28, co-founder of Nixon Watches, an
action-sports-oriented watch company in Encinitas, California.

But, Chad, we plead. Isn't Nixon's customer base
precisely the one marketers mean when they use the word
"extreme?" These are young, hip, hyperkinetic surfers and
snowboarders. They're lifestyle icons, trendsetters. Why,
they're so extreme, we'd even call them X-treme.

But not DiNenna: "My partner [Andy Laats, 32,] always says,
`If you had a bar and called it Winners, there'd be no one but
losers inside.' " Apparently by the same token, true
extremists aren't enthralled by X-Games T-shirts and Boston
Market Extreme Carver sandwiches.

Meanwhile, mainstream consumers who are supposed to delight in
images of street-luging, bungee-jumping, sky-surfing daredevils in
ads aren't necessarily trying these antics themselves.
"I'm sure less than 5 percent of the population has ever
participated in any of these activities," says marketing
expert Susan Mitchell, author of American Generations: Who They
Are, How They Live, What They Think (New Strategist, $79.95,
607-273-0913). Ditto for other stereotypical trappings of
Generation X-cess: full-body tattoos, illegal drug use, blue
lipstick. "It's an image," explains Mitchell.
"The real Generation X is getting married and raising
families."

Tuned In

Welcome to the fin de siÃ¨cle, where anything
over-the-top is susceptible to overplay--and where the cutting edge
can whip around like a chainsaw on the loose. It's a world
where your mother's favorite nail polish company makes a line
of blues and greens, and your 2-year-old niece rips around in her
own motorized "X-treme Machine." "I recently worked
on a middle-aged man, and his kids were telling him not to
do it," laughs tattoo artist Karen Slafter, 32, co-owner of
Incredible Ink in Austin, Texas.

If the current fringe fever seems a little far-out--or at least
far-reaching--it's not your imagination. "Young people
have always been interested in living at the edge. It's a time
in life when people are experimenting, when they don't know any
boundaries," observes James Twitchell, professor of English at
the University of Florida, Gainesville, and author of Lead Us
Into Temptation: The Triumph of American Materialism (Columbia
University Press, $19.99, 212-666-1000). "But in the '50s
and [early] '60s, for example, [such forays into the fringe]
were pretty much hidden. Nobody really cared."

Young people did their thing while the culture at large went
about its business: There was the establishment and the
anti-establishment. Today, Twitchell notes, the ethics of extreme
and excess have become guiding forces in the entire culture.
"[Fringe] culture is the center of fashion, the center of
music--it's everywhere," he says.

Why? In part, it's because shock imagery makes memorable
advertising. As the media universe proliferates, it becomes harder
and harder for marketers to grab attention. Extreme images break
through the clutter.

But Twitchell also notes that marketers haven't simply
amplified their techniques--they've also switched their focus.
"The [adolescent and young adult] audience which had been
[marginalized] is now of great interest to advertisers,"
Twitchell says. "Advertisers have realized they don't want
to reach the person who's already consuming; they want the
person who hasn't yet developed a brand loyalty."

As advertisers--and the corresponding media--try to reach out to
young audiences, things that once might have been considered
bizarre, kooky, shocking or profane are now beamed into American
homes with all the wholesome legitimacy of mainstream culture.
It's enough to turn your grandmother's hair
purple . . . or any other semi-permanent color
of her choice.

Core Or Middle?

However, uh, thrilling it is to have your counterculture
lifestyle validated by the mainstream, that thrill is certainly
mitigated by simple exhaustion. Suppose you've gone to the
considerable trouble of creating a line of nail polish and
lipsticks in "alternative" colors--as Anna and Sarah
Levinson (ages 22 and 19, respectively) of Ripe Inc. in Los Angeles
have done. Just three years later, competitors both large and small
are trampling all over your niche, rendering your pastel blues and
gunmetal greys practically pedestrian. How do you respond?

By innovating at whiplash speed, of course. "We have to be
much more phenomenal today than we were three years ago," says
Anna. "Just the fact that a color isn't part of the
traditional [lipstick and nail polish] palette isn't
enough." What does make the cut? For nail polish,
it's iridescent shades to wear alone or on top of other colors,
a matte finish that gives metallics and cremes new polish, and
fashion colors with a twist: "We never look at another
company's colors and say `We've got to do
that,' " Anna explains. "We'll take a color
that's out there and make it our own. We always ask `How can we
make this color better?'"

The Levinsons appreciate the fact that the mainstream popularity
of "alternative" cosmetics has expanded the market for
Ripe's goods. But they also acknowledge that it's made fast
work of what was once the newest thing on the block. "The
normal green [nail polish] isn't cutting it anymore," Anna
says without irony.

Indeed, mainstream acceptance can make the cutting edge seem,
well, dull. It's not just that your adolescent impulses toward
rebellion are quashed. It's that the mainstream tends to
sanitize the "alternative" until it's little more
than a gimmick.

Derek Chung, 29, a veteran of San Francisco's rave scene and
co-founder of Late Train, a Web site devoted to local late-night
culture, recognizes what he calls the "style and some of the
symbols" of alternative culture in mainstream marketing.
"Advertising has used some of the music and visual design from
rave culture," Chung notes, "but of course, ideas about
independent community, decriminalization of drugs, civil liberties,
and the breaking down of personal and social barriers are not
included."

Of course not. Mainstream companies can't alienate people by
presenting alternative viewpoints that are actually alternative.
And, conversely, companies that want to keep their edge sometimes
have to keep their businesses from veering too close to the middle.
DiNenna and Laats, for example, have decided to sell their watches
only in what they call "specialty" surf, skate and
snowboard shops--venues that might reach a limited market, but in
which Nixon's authenticity actually means something.

The Alternative Scene

The relationship between the leading edge and the bulging middle
is uneasy at best. Yet, it may also be a necessary one. If your
entrepreneurial goal is to reach a wide market--but your
entrepreneurial resources dictate a modest start--homing in on a
(potentially alternative) niche may be your best shot. If your
demographic allegiance is to the so-called Speed Generation, so
much the smarter.

Similarly, entrepreneurs with an edgy perspective don't have
to restrict themselves to a small circle of like-minded clients.
Tattoo artist Slafter, for example, has won a reputation for
innovative, artistic work that makes her popular with the local
cognoscenti. But she's also known for working well with the
less-than-bold.

"A lot of young girls don't want to go to some big
biker guy and expose themselves [in order to get a tattoo],"
Slafter explains. "And the pain factor is important to people,
too--you don't have to murder them to give them a tattoo."
While some in the body art industry are becoming increasingly
outrageous--surgically implanting items like BB's under their
clients' skin--Slafter sees herself going in the other
direction: "We have a nice, comfortable place, with faux
finishes on the walls that the artists did themselves and a small
art gallery where we feature local work."

Walking the line between hip and hapless takes some
maneuvering--and you don't always know which way to lean. When
the principals at San Clemente, California-based World Oceans
Media--publishers of Launch Wakeboard, Pit Bodyboard and
Wave Action Surf magazines--decided to reorganize and launch
their own Web site, they chose the URL http://www.e-xtreme.com and
changed the company name to e-X Inc. Co-founder Tracy Mikulec, 34,
admits to some trepidation about associating the company with the
"E-word."

"The word `extreme' does tend to be overused by the
mainstream," Mikulec says, "but our main goal is to reach
as many people as possible--and the fact is, a lot of people know
what `extreme' is."

More important, says Mikulec, who founded the business with Jake
Knight, 31, is the company's ability to walk the walk--to stay
in touch with a demographic that isn't served by more polished,
upscale publications. "We're not a big publishing group
targeting wealthy, literary people who happen to surf on
weekends," Mikulec says. "We're in the [surf] shops,
not on newsstands where the mainstream is looking for magazines.
Most of our submissions are freelanced, so we get all the young
talent to put their own spin on things. We're understaffed, so
we do everything ourselves. We get a raw product that doesn't
have all the checks and balances associated with bigger
publications--and that's good. Being loose has resulted in at
least a couple of disasters, but overall, I think it works to our
advantage."

It's Up To You

In the end, Mikulec's observation may be the keenest of all.
Whether your intention is to go mainstream or swim upstream, you
need quick moves and the attention span of a gnat. You also need to
know this: Staying ahead of the curve isn't a function of
reading reports, performing research or co-opting someone
else's groove.

It's about being in it--having the artistic vision of
Slafter or the playful genius of the Levinsons or the
"loose" flexibility of e-X or the dogged rebelliousness
of DiNenna. If you're reading this story to find out what the
latest thing is and how to plug it into your business, consider
yourself done. On the other hand, if you have something to say--and
the nerve to say it--get started.